This invention relates to sulfamoyl chlorides which are useful as intermediates for preparing sufamides and pyrrole sulfonamides which are useful as agricultural chemicals and particularly as herbicides.
The sulfamides of this invention are compounds of the formula ##STR1## wherein R.sub.10 and R.sub.9 are as defined below.
The pyrrole compounds are disclosed in copending U.S. application Ser. No. 244,172, now U.S. Pat. No. 3,368,067, and have the general formulae ##STR2## wherein R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, NO.sub.2, CN, C(O)CCl.sub.3, SO.sub.2 R.sub.11, C(O)R.sub.5, or CO.sub.2 H;
R.sub.2 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, Cl or Br; PA1 R.sub.4 is H, C.sub.1 -C.sub.4 alkyl, cyanoethyl, C.sub.5 -C.sub.6 cycloalkyl, benzyl, phenyl substituted with Cl or NO.sub.2, or C(O)R.sub.6 ; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyll, C.sub.1 -C.sub.4 alkoxy, or NR.sub.7 R.sub.8 ; PA1 R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.9 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.11 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.10 is ##STR3## X is CH.sub.3 or OCH.sub.3 ; Y is H, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3, Cl, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3 or CF.sub.3 ; PA1 Y.sup.1 is H, CH.sub.3, OCH.sub.3, Cl or OCH.sub.2 CH.sub.3 ; and PA1 Z is CH, N, CCH.sub.3 CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl, CCl, CBr or Cf; PA1 (1) when R.sub.4 is C(O)R.sub.6, t-butyl or phenyl substituted with Cl or NO.sub.2, then R.sub.1 is H or C.sub.1 -C.sub.4 alkyl and R.sub.1, R.sub.2 and R.sub.3 cannot be s-butyl or isopropyl; PA1 (2) R.sub.1, R.sub.2, R.sub.3 and R.sub.11 cannot be t-butyl; PA1 (3) in Formula Ia, when R.sub.1 is NO.sub.2, then R.sub.1 cannot be in the 5-position; PA1 (4) in Formula Ia, when R.sub.1 is not in the 5-position, R.sub.2 and R.sub.3 are other than H, and R.sub.1 must be other than H unless both R.sub.2 and R.sub.3 are H; PA1 (5) in Formula Ia, R.sub.3 cannot be Cl or Br; PA1 (6) in Formula Ib, R.sub.1 cannot be C(O)CCl.sub.3 ; and PA1 (7) in Formula Ib, when R.sub.3 is Cl or Br, then R.sub.3 is in the 3-position and R.sub.1 is in the 5-position and R.sub.1 cannot be H or C.sub.1 -C.sub.4 alkyl. PA1 R.sup.1 is Cl, (CH.sub.3).sub.2 N or ##STR6## R.sub.10 is ##STR7## X is CH.sub.3 or OCH.sub.3 ; Y is H, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3, Cl, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3 or CF.sub.3 ; PA1 Y.sup.1 is H, CH.sub.3, OCH.sub.3, Cl or OCH.sub.2 CG.sub.3 ; PA1 Z is CH, N, CCH.sub.3 CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl, CCl, CBr or CCF.sub.3. PA1 (1) Compounds of the generic scope wherein R.sub.9 is H or CH.sub.3 and R.sup.1 is Cl; PA1 (2) Compounds of Preferred (1) wherein Y is CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and Z is CH or N; PA1 (3) Compounds of Preferred (2) wherein Y.sup.1 is H, CH.sub.3 or OCH.sub.3 ; PA1 (4) Compounds of Preferred (1)-(3) wherein R.sub.9 is H; and PA1 (5) Compounds of Preferred (4) wherein ##STR8## PA1 R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, NO.sub.2, CN, C(O)CCl.sub.3, SO.sub.2 R.sub.11, C(O)R.sub.5, or CO.sub.2 H; PA1 R.sub.2 is H or C.sub.1 -C.sub.4 ; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, Cl or Br; PA1 R.sub.4 is H, C.sub.1 -C.sub.4 alkyl, cyanoethyl, C.sub.5 -C.sub.6 cycloalkyl, benzyl, phenyl substituted with Cl or NO.sub.2, or C(O)R.sub.8 ; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, or NR.sub.7 R.sub.8 ; PA1 R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.2 alkyl; and PA1 R.sub.11 is C.sub.1 -C.sub.4 alkyl; PA1 (1) when R.sub.4 is C(O)R.sub.6, t-butyl or phenyl substituted with Cl or NO.sub.2, then R.sub.1 is H or C.sub.1 -C.sub.4 alkyl and R.sub.1, R.sub.2 and R.sub.3 cannot be sec-butyl or isopropyl; PA1 (2) R.sub.1, R.sub.2, R.sub.3 and R.sub.11 cannot be t-butyl; PA1 (3) in Formula Ia, when R.sub.1 is NO.sub.2, then R.sub.1 cannot be in the 5-position; PA1 (4) in Formula Ia, when R.sub.1 is not in the 5-position, R.sub.2 and R.sub.3 are other than H, and R.sub.1 must be other than H unless both R.sub.2 and R.sub.3 are H; PA1 (5) in Formula Ia, R.sub.3 cannot be Cl or Br; PA1 (6) in Formula Ib, R.sub.1 cannot be C(O)CCl.sub.3 ; and PA1 (7) in Formula Ib, when R.sub.3 is Cl or Br, then R.sub.3 is in the 3-position and R.sub.1 is in the 5-position and R.sub.1 cannot be H or C.sub.1 -C.sub.4 alkyl.
and their agriculturally suitable salts; provided that
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs such as soybeans, barley, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such crops by killing or inhibiting the growth of undesired vegetation, with herbicidal compounds such as those described above, is one way of improving this efficiency.
Useful intermediates, such as those of the instant invention, facilitate the production of the desired herbicidal compounds.
German Pat. No. 2,439,087 discloses the following compound: ##STR4##